The Milwaukee Bucks reportedly explored the possibility of acquiring Victor Oladipo from the Indiana Pacers on the basis of his existing rapport with Giannis Antetokounmpo, according to The Athletic's Shams Charania, Eric Nehm and Sam Amick.
"However, this offseason consisted of Antetokounmpo spending time with Indiana Pacers two-time All-Star Victor Oladipo, working out and hanging out abroad, sources said," the report said. "It is one of the major reasons the Bucks pursued Oladipo and made an offer for him in the offseason, according to sources."
The report came after Antetokounmpo announced his plans to sign a supermax extension with the Bucks:
Bleacher Report's Jake Fischer reported Nov. 25 that Oladipo "was discussed in numerous trade scenarios, sources said, but Indiana ultimately declined Milwaukee's advances." One hypothetical trade package included Donte DiVincenzo, George Hill and the No. 24 selection in the 2020 NBA draft.
Especially since it didn't adversely impact the likelihood of Antetokounmpo staying in Milwaukee, failing to land Oladipo may not have been that bad for the Bucks.
Adding the two-time All-Star would've meant sacrificing roster depth while almost certainly taking on a big financial commitment since Oladipo's due to hit free agency in 2021. That would've been a steep price for a player who hasn't regained his best form since suffering a ruptured quad tendon in January 2019.
Oladipo averaged 14.5 points and 2.9 assists while shooting 39.4 percent from the field and 31.7 percent from long range in 19 regular-season games upon returning to the court in 2019-20. His playoff performance was only marginally better as he averaged 17.8 points and 2.5 assists in a first-round sweep by the Miami Heat.
Even before the injury, his electric 2017-18 season looks more and more like an outlier as he wasn't replicating the same kind of production to open 2018-19.
Perhaps Oladipo will have a massive 2020-21 and prove all his skeptics wrong, at which point the Bucks would be kicking themselves that they couldn't work something out with the Pacers.
Barring that outcome, it's hard to see how Oladipo would've meaningfully improved Milwaukee's odds of reaching the NBA Finals if he had joined the squad this offseason.